Discovery of Michael reaction acceptors from the leaves of Ailanthus altissima by a modified tactic.

Autor: Duan ZK; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Guo SS; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Ye L; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Gao ZH; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Liu D; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Yao GD; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Song SJ; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China., Huang XX; Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province China; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province China; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China. Electronic address: xiaoxiao270@163.com.
Jazyk: angličtina
Zdroj: Phytochemistry [Phytochemistry] 2023 Nov; Vol. 215, pp. 113858. Date of Electronic Publication: 2023 Sep 13.
DOI: 10.1016/j.phytochem.2023.113858
Abstrakt: Structural characteristics-guided investigation of Ailanthus altissima (Mill.) Swingle resulted in the isolation and identification of seven undescribed potential Michael reaction acceptors (1-7). Ailanlactone A (1) possesses an unusual 1,7-epoxy-11,12-seco quassinoid core. Ailanterpene B (6) was a rare guaianolide-type sesquiterpene with a 5/6/6/6-fused skeleton. Their structures were determined through extensive analysis of physiochemical and spectroscopic data, quantum chemical calculations, and single crystal X-ray crystallographic technology using Cu Kα radiation. The cytotoxic activities of isolates on HepG2 and Hep3B cells were evaluated in vitro. Encouragingly, ailanaltiolide K (4) showed significant cytotoxicity against Hep3B cells with IC 50 values of 1.41 ± 0.21 μM, whose covalent binding mode was uncovered in silico.
Competing Interests: Declaration of competing interest No declaration of interest statement exists in the submission of this manuscript.
(Copyright © 2023. Published by Elsevier Ltd.)
Databáze: MEDLINE
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